Chris Guillebeau: Side Hustle Your Way to Financial Freedom

Chris Guillebeau is the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, Born for This, and The Art of Non-Conformity.

Chris travels the world and writes for a small army of remarkable people at, or you can listen to his daily podcast, Side Hustle School, at

Favorite Success Quote

“Once in a while it really hits people that they don’t have to experience the world in the way they have been told to.” -Alan Keightley

Key Points

1. You Don’t Have to Live the Way You Are Told 

Go to school, get good grades, attend college, find a cushy job with nice benefits, buy a house, get married, have 2.5 kids, die.

That’s the script that most of us have been told to follow.

We’ve been fed a steady diet of lies and misinformation that make us believe that there is only one way to approach life, that there’s a select set of goals and ambitions that are acceptable and the rest are heresy.

Luckily for you and me… There’s more to life than what we were told growing up.

Since the inception of the internet, it’s easier now than it’s ever been in human history to create a sustainable income doing something that you love.

It’s easier than it’s ever been before to shrug off the expectations and “should’s” of society and to go about life in our own way.

You don’t have to do what anyone else tells you to do.

If you want to go to college, get a job, get married, and buy a house in the hills, then great!

If you don’t, if you want to drop out, travel the world, start an online business, and live the expat lifestyle, you can do that too.

You have the power to decide who you want to be and what you want to do.

You have the ability to decide for yourself what kind of life you want to live.

Make the most of it.

2. What One Man Can Do Another Man Can Do  

In a world that glamorizes the end result without giving so much as a second thought to the process, it’s easy to look at the successes of others and believe that their accomplishments are out of your reach.

But they were people just like you.

Grant Cardone, Gary Vaynerchuk, and yes, Chris Guillebeau are all just normal people who have done extraordinary things.

There’s nothing special about them, they didn’t have any unique advantages that you don’t have, they were just normal everyday guys who applied proven principles and tactics to achieve extraordinary results.

Whatever it is that you want to achieve in this life, it’s possible, and the first step on your path to making it happen is to acknowledge that it’s possible.

What one man can do, another man can do. If it’s been done before it can be done again.

Always remember this and always keep your head up.

3. A Side Hustle is an Asset 

One of the biggest mistakes that people make when it comes to building a side hustle is to think that a “Side Hustle” is the same thing as a part-time job.

There’s nothing wrong with freelancing or working part-time, but at the end of the day, these endeavors all require the same thing… Your time.

No matter how highly paid you become, anything that directly requires your time to make money is a part time job, not a Side Hustle.

A side hustle is an asset, it’s something that can make you money while you sleep, it’s something that you can set and forget.

It’s something that generates revenue without consuming your life.

4. Your Hustle Isn’t that Big of a Deal 

I know countless individuals who work jobs that they love.

They decide to build a side hustle, quite simply, because they want the extra cash.

After weeks of brainstorming and agonizing over potential paths they could take, they eventually collapse into a puddle of nerves and anxiety.

Not because the task ahead of them is so monumental, but because they have put their side hustle on a proverbial pedestal. They turned it into something that it wasn’t.

A side hustle is nothing more than a fun project that you work on in your spare time to generate extra revenue.

That’s it.

You don’t have to be passionate about it as long as you enjoy it.

You don’t have to make 6-figures with it (unless you want to).

You don’t have to turn it into anything of significance.

It’s just a way to make extra income doing things you like.

So don’t worry about finding your “One Thing”. Make a list of 10 different side hustles, try each one for 2-3 weeks and if you don’t like it, throw it in the garbage and start the next one.

This is an experiment, treat it as such.

5. Just Get Started 

No matter what goal you are pursuing, whether it’s to travel the world, find your dream job, or simply start a side hustle to earn an extra $2,000 a month, the first step will always be the hardest.

You will always second guess yourself, over analyze, and eventually, give up if you don’t take the first step and dive into the water head first.

Just get started.

As simple as it sounds, it’s the key to about 90% of success.

Just get started, take the first step, write the first word, buy that domain, talk to that girl, do whatever it is that you need to do to move towards your dreams.

Get started today.

Because tomorrow you will wish you had started yesterday.

Chris’ Books

1. The Art of Non-Conformity

2. The $100 Startup

3. The Happiness of Pursuit

4. Born for This

5. Side Hustle

Connect with Chris Guillebeau

Next Steps

We’re on a mission to impact a million men with powerful life changing content. If you enjoyed this article, please share it with your friends on your preferred social network on the left. I spent a ridiculous amount of time creating this article for you and with your support, we can impact the world together.

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